Triethylamine → HCID 22633005, compound

HRID 2270190Notes

Reaction equation

HRID 2270190 reaction equation
C(N=C=NCCCN(C)C)C.C1C=CC2N(O)N=NC=2C=1.[OH:22][C:23]1[CH:40]=[CH:39][C:26]([NH:27][C:28]2[CH:36]=[C:35]([F:37])[C:34]([F:38])=[CH:33][C:29]=2[C:30]([OH:32])=O)=[CH:25][CH:24]=1.Cl.[CH2:42]([O:49][NH2:50])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(N(CC)CC)C>ClCCl.CCOCC>[OH:22][C:23]1[CH:24]=[CH:25][C:26]([NH:27][C:28]2[CH:36]=[C:35]([F:37])[C:34]([F:38])=[CH:33][C:29]=2[C:30]([NH:50][O:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:32])=[CH:39][CH:40]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 22632923HCID 22632923, compound

Product 1

HCID 22633005HCID 22633005, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide (EDCI, 0.22 g, 1.1 mmol) and HOBt (0.17 g, 1.1 mmol) were added to a solution of crude 2-(4-hydroxyanilino)-4,5-difluoro-benzoic acid (Example M, 0.265 g, 1.00 mmol) in 70 mL of dichloromethane at 0° C. After 1 hour, O-benzylhydroxylamine hydrochloride (0.176 g, 1.1 mmol), and triethylamine (0.15 mL, 1.1 mmol) were added, and the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with 100 mL of ether and washed with water and 0.1N HCl, water, and brine, dried over sodium sulfate. Solvents were evaporated to give 0.35 g of the title compound as a crude solid.

Workup

  1. washwashed with water and 0.1N HCl, water, and brine
  2. dry with materialdried over sodium sulfate
  3. customSolvents were evaporated

Sources & evidence

ORD record
ord-4746e38d9d8c47d79963565d1b25e6b4
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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